


One Night Between Friends

by oneshotsbygabby



Category: Supernatural
Genre: Cunnilingus, Explicit Sexual Content, F/M, Friends to Lovers, Getting Together, Light Angst, One Night Stands, Oral Sex, Pining, Pining Dean Winchester, Reader-Insert, Smut
Language: English
Status: In-Progress
Published: 2018-12-17
Updated: 2018-12-17
Packaged: 2019-09-20 22:52:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,075
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17031477
Author URL: https://archiveofourown.org/users/oneshotsbygabby/pseuds/oneshotsbygabby
Summary: You and Dean have been friends for a long time. There can't be more there...can there?





	1. Chapter 1

**Author's Note:**

> Based on this imagine: [Imagine having a few beers and you wind up admitting to the Winchesters that you’ve never had good sex, and they’re just buzzed enough to tell you they’ll fix that](http://thranduilsperkybutt.tumblr.com/post/132193711313/warnings-drunkenness-nsfw-mentions-gif-source) with a change. Instead of it being both Winchesters, it's just Dean. And this is a WIP, I don't know how many chapters it'll be, but it's something I'm working on little by little.

You had known the Winchesters a long time, being Bobby Singer's daughter and everything, so they were practically family. You had grown up hunting side-by-side with Sam and Dean, and you and Dean had been close your entire life. You were just a couple of years younger than Dean, which made you two years older than Sam, but you and Dean seemed to get each other like no one else could.

Which was why it didn't surprise you that you were sitting across the table from Dean that night, at your dad's house, nursing a beer. Life wasn't going that great for you right now; another break-up, which wasn't too bad, but that made three in the last year.

When you turned eighteen, you gave up hunting, but the last few years you were thinking about returning to it. While your dad was cool with you giving it up for a normal life life, things were different once you knew what was out there in the dark.

When Sam and Dean popped in to see your dad, and Sam had disappeared to get some sleep, it left you and Dean to catch up. And you hated it.

Because while you and Dean _used to_ be close, things had gotten in-between you the last few years. Maybe it was the string of exes you seemed to have, or maybe it was you, or maybe it was the job. Friendships and romances were hard to keep up when you were a hunter.

"I'm sorry about the break-up, Y/N," Dean said, and it almost took you by surprise. He was actually showing some kind of feelings different than the Dean you knew. "You deserve better than that."

You shrug, "I'm not too broken up about it. He was an ass anyway. And besides that, the sex wasn't even good."

It may have been oversharing to some people, but you and Dean had always talked to each other about everything. It didn't escape your notice, however, how Dean was just kind of watching you. It was weird.

"Then why stay with him as long as you did? I mean, that wasn't the only thing, right?"

You shrug again, "I don't like being alone. Not after all the shit I've seen. I think I stayed with him just because I didn't want to be by myself."

You take another swig of your beer before saying, "Besides, bad sex? Pretty normal for me. I don't think I've ever had any good sex."

He gaped at you for a moment, "You're kidding, right? Not even once?"

You shrug; it's not a big deal. There's more to a relationship than just sex, and Dean laughed when you told him this. You knew Dean Winchester, and he knew there was more to a relationship than just sex, although you weren't sure that he'd ever be with anyone if there was bad sex involved.

There were a few moments of silence, which almost worried you, but then you said, "Hey, it's no big deal. Sorry for oversharing. I seem to be excellent at that."

You know your ex left you because you seemed to be more cynical than most people were, which didn't surprise you. Growing up the way you had, losing your mom the way you had, the life you lead...not many people survived that kind of thing. Not completely, anyway. You were never going to _not_ know that there were real monsters out there, and it took a toll on your disposition.

You didn't mention the break-up again, and Dean didn't seem to want to talk about heavy subjects. You just sat there and traded stories about what you'd been up to and that seemed to be just fine with the two of you.

Five beers later, you were pleasantly buzzed and even though it took a great deal more for Dean to get that way, he seemed to be heading that direction. As you took the last drink out of that bottle, you looked up to see Dean watching you.

"What's the matter?" you ask. "Is there something on my face?"

He shook his head, "No, nothing like that. I just...I can't get over what you said. No good sex, not even once?"

You stifled a laugh and then said, "Hate to break it to you, Dean, but not every guy is a sex god like you are." You shot a wink his way and enjoyed the blush that came to his cheeks. You should have known something was up; Dean Winchester just did _not_ blush like that.

You wished you could've grown up half as self-confident as Dean had; he had the looks, he knew it, and while he wasn't cocky, he came off as just really confident. He was a great guy, really knew how to treat women, and there had been a time in your life that you had been in love with him.

You, on the other hand, just kind of let things happen, but you put up with assholes because you weren't sure if you could get any better. You took what you could get, and while you weren't exactly down on yourself all the time, you just had no confidence. You knew the reason Dean got as many women as he did was that damn self-assurance.

"Yeah, but why put up with it?" Dean asked, and you realized he wasn't going to let the subject go. "Why on Earth would you stay?"

"Because I'm not special, Dean," you mumble, not sure if you want him to hear you. "You and Sam, you guys are confident. I'm not. I don't matter; I've never mattered. At least, not to anybody important."

Dean had been your first kiss, back when you were thirteen and he was fifteen, and it was just because you wanted to know what it felt like and Dean was always up for making you happy. You hadn't let him know you were in love with him back years ago because you knew he didn't feel the same way. In all honesty, you weren't sure that you had ever gotten over him.

He reaches across the table and grabs your hand, as his amazingly green eyes study you. "Don't ever say that, Y/N. You're more special than you know."

You didn't want to turn this into a pity party, so you just nod. He takes the last drink of what's in his beer bottle before saying, "Besides, if you've never experienced good sex...I could help with that. I mean, if that's what you want."

You gape a bit at that. Then, after a few seconds of doing that, you look him straight in the eye. "Are you suggesting what I think you are?"

Dean licks his lips before nodding, "Yeah. If you want. We could have one night, a no strings attached kind of situation."

You wanted more with Dean Winchester. You loved him, had for quite a while, and since you'd been sitting here catching up with him, those feelings started coming back. But he was offering you something you've never gotten before -- but were you actually going to act on it?

Finally, decision made, you nod slightly, saying, "If that's what you want, then yes. Yes please."

He was out of his chair in an instant, over and standing beside you, as he pulled you up out of your chair. He caresses your cheek and you tilt your head just a bit so you can stand up on your tiptoes and capture his lips with your own. The kiss starts off soft, a chaste, dry meeting of the lips, but it isn't long before his tongue is sliding across your lower lip, silently asking for access. You grant it to him, angling your head just right so he can deepen the kiss. Dean tastes like beer and mint and something that can be just described as pure _Dean_ , and you love it. You wrap your arms around his neck and he wraps it around your waist.

You stand there, making out with him, for what seems like forever. You love the way he tastes, the way he feels, his hard body against yours, and you want more. _God_ , do you ever want more. So you break the kiss and grab his hand, leading him to your old bedroom. It's the bedroom that you've been staying in while visiting your dad, and it's at that moment that you're grateful that you decide to put in a full-sized bed.

Once inside the room, you pushed the door closed and then leaned up against it. He cupped your cheek as he kissed you again, rubbing his thumb back and forth against your cheekbone. You loved the way he felt, his lips on yours -- it already felt better than anything anybody had ever done to you, and you were just kissing. You couldn't wait to see what it felt like when you actually got to the good stuff.

Dean breaks the kiss just briefly enough to rip your t-shirt from your body, and then disposes himself of his shirts as well, throwing them on the floor. He leans down to capture your lips one more time as you run your nails up and down his chest. God, he was gorgeous, and felt amazing under your fingers.

He let out a soft groan while you did that, and then helped you dispose of your other clothes, as he got rid of his, and then carried you over to the bed. He laid you down there, leaning over you and kissing you once more, letting your tongues tangle together.

Breaking the kiss, he started kissing down your body, starting with your jaw, placing a kiss right underneath your ear, before leaving nips and open-mouthed kisses down your neck, to your chest, taking the time to swirl his tongue around one nipple and then the other, caressing them both as he started his journey south once more.

When he tried to coax your legs open, you were nervous. You opened them, and he leaned down, sucking a bruise into your stomach and over by your hip, and you noticed where he was heading, but you started to get nervous. He wouldn't really...would he?

He noticed your trepidation, however, so he looked up at you. "What's wrong, sweetheart?" he murmured.

You were certain that he could see the fear and anxiety that was written all over your face, even though you tried to act like you had it all together, so you just said, "Um...you don't have to go down on me. Nobody ever has, and I --"

"Nobody's ever done that for you?" Dean looked shocked. You just shrug your shoulders.

"It's not a big deal, Dean, really," you say. "I can live without it -- I _have_ lived without it."

"I want to do this for you. Trust me, Y/N, it's for me just as much as it is for you. If you don't want me to, I won't, but I really want to try, if that's okay...?"

He let the words trail off, ending in a question, but you decide what the hell, so you open your legs and Dean smirks before getting in-between them. He leans over and inhales your scent before his green eyes glance up into yours.

You nod slightly, telling him that it's okay, and he leans down and licks a stripe up your pussy. Lying on his stomach, he spreads your lower lips before fucking his tongue inside of you, his nose brushing against your clit.

You groan; you'd never felt a sensation like this before, but you can easily tell that you could fall in love with it. Your hips start moving, almost by themselves, and you're grinding against his mouth, but then you realize what you're doing and get nervous. You stop and Dean glances up at you.

"It's okay," he chuckles. "I like it. Keep doing what you were doing, you taste so fucking good, sweetheart."

He goes back to eating you out, this time he wraps his lips around your clit and sucks lightly as he inserts two fingers inside your heat, thrusting them in and out. It feels so good, and you start to lose yourself, and he licks at your clit, softly at first but then a little harder and faster, and you can feel your orgasm, it's so fucking close, it's getting closer and closer...

"Cum for me, baby," Dean says, noticing how close you are. He crooks his fingers inside of you, rubbing them deliciously over your g-spot, and then wraps his lips around your clit one more time. Sucking on it hard this time, it sends you over the edge and you cry out your release.

He laps up your juices and cleans them off his fingers before climbing up your body and capturing your lips in a kiss. You can taste yourself on his mouth, and instead of being turned off by it like you thought you would, it turns you on. Immensely.

You reach down and grab ahold of his cock, running your hand up and down the shaft a couple of times before saying, "I need you, Dean. I need to feel you inside of me."

"That sounds like an excellent plan," Dean says. Deciding that you want to ride him, you get up, and throw him down on the bed on his back. He chuckles as you do so but doesn't say anything, he just lets you do what you please. You jack his cock a couple of times before easing yourself down onto it slowly, taking him inch by inch. It's been a while since you'd been intimate with anyone, and Dean is bigger than anyone you've ever been with, so you take your time.

Once he's bottomed out inside of you, your hips flush against his, you start to move slowly, taking your time to grind against him. You lean down and capture his lips with your own, and you kiss him as you speed up a little bit. You bounce on his cock as you press your hands on his chest, using that as leverage to hoist yourself up and down. He feels so good, and as you move faster, you never want this to end.

"That's right, Y/N," Dean moans, "take your pleasure, baby. You're so fucking hot when you take what you want."

You groan as he talks, his words getting a little more graphic as he goes on, and you feel like you're right on the edge. You're so close to cumming, you just need a little push, and Dean can tell, because he says, "Touch yourself, baby. I want to feel you cumming around my cock...oh God, it's going to feel so fucking good."

Reaching down, you start fingering your clit hard and fast, and it isn't long before you're cumming around him. He thrusts up into your pussy once, twice, and then a third time before he's losing it inside of you. He groans loudly as he cums inside of you.

There's a sheen of sweat on both of your bodies and you collapse on his chest, feeling boneless after that amazing orgasm you just had. You manage to climb off of him, lying down beside him on the bed and pulling a sheet over your body.

"You can stay tonight, if you want," you say, feeling the sleepiness start to overtake you. "It's okay with me."

And you don't see the look on Dean's face, the look that says that he never wants this to end.


	2. Chapter 2

**Summary for the Chapter:**

> After your one-night stand, you and Dean talk to figure out what you want from one another.

"Why don't you just tell her how you feel, Dean?" Sam was asking his brother. They were in a crappy little motel in a small town about an hour and a half from your dad's house, where you were living.

It had been a couple of months since your encounter with Dean. Two months since your little one-night stand, since your no strings attached sex. And he hadn't been able to stop thinking about it ever since.

He wanted you romantically. Not only had the two of you grown up together, but as you started getting older, he started noticing how beautiful you were. How much he wanted to be with you. When he had the one-night stand with you a couple of months ago, he was only kidding himself, thinking all it could ever be was one night.

"I can't," Dean said dejectedly. "She doesn't want me that way."

"How do you know that, though?" Sam asked him, watching his brother closely. "Have you actually used your words and talked to her about it?"

The truth was no, of course he didn't. He wasn't ready to get his heart broken.

And Dean was a heart _breaker_ , he had been for a really long time. He left a girl in every city, and that was the way it'd been since he was a teenager. He wasn't one to settle down; after all, hunting wasn't conducive to keeping up romantic relationships.

But you weren't _just_ some girl, either. You'd known the boys since you were seven years old, and he had seen you blossom from a little duckling to a beautiful swan. He'd wanted you for a really long time, but you had decided to give up hunting and then gone on to try and date normal guys. If it hadn't been for Bobby being your father, you wouldn't have been around hunters at all.

Dean didn't think he deserved you. He knew all his faults and flaws, and he also knew that what he wanted and what he got were normally two separate things. He _wanted_ you, there was absolutely no doubt about that, but at the same time, you deserved better. These days, with everything that had happened in his life, he was just a broken-out shell, and you deserved someone a little bit livelier.

"I can't," Dean said, answering Sam's question. "She deserves better."

Sam rolls his eyes before saying, "Well, we just finished up the case. The ghouls are decapitated and we're ready to go on to the next town." He picks up his phone and shoots you a text, almost surprised that your response doesn't take that long, either. "There. All done. We're going to spend a couple of days at Bobby's."

"Why, Sammy? Why would you do that?" Dean couldn't figure out if he was relieved or angry. Relieved because he was able to see you again, or angry because of the way Sam went about it.

"The two of you need to talk this shit out, Dean," was Sam's reply. "I am not spending any more time with this lovesick fool version of you, and from what I hear, she hasn't been herself lately, either."

Which was true, and if you ever found out that Sam told his brother that, you'd really have his ass. Because it was true; you had had a crush on Dean when you were younger, and it was one that had never fully gone away. But Dean was a heartbreaker, and you had never acted on those feelings. Besides that, if you were being totally and one hundred percent truthful, you didn't want to put your heart on the line and get it broken.

A lot like Dean's reasoning.

The ride to Sioux Falls was a quiet one, a lot more quiet than normal. Sam and Dean weren't bickering like they usually did, nor were they even talking. Sam had a book on his Kindle and Dean drove down the road. Anxiety was starting to overtake him; he wasn't sure what he was going to say to you. Truth be told, he was just really fucking nervous.

It was almost nine o'clock when they arrived at your dad's house, and Bobby wasn't home. He had gone on a hunt of his own and had been gone almost a day. You were actually pretty happy to have the company; when Sam texted you and said that you and Dean really needed to talk, you figured you'd do it just because you were bored out of your mind and a bit lonely.

You heard the Impala pull up. You had been vegging on the couch, some mindless TV show that you were only half-paying attention to on the television when you heard it. You jumped up and met them outside.

"Hey, Y/N, it's good to see you," Sam said to you with a big smile on his face. "How're you doing?"

You nod, "I'm okay. Bored out of my mind, but okay."

"Where's your dad?" Dean asked, speaking for the first time. That partly worried you; they had been here for a good five minutes before he even looked at you.

"He's on a hunt. He should be back in a few days."

Dean looked at you, and the tension was so thick you could cut it with a knife. Deciding to get it over with already, you looked at Dean and said, "We need to talk."

He shot Sam a dirty look before he followed behind you. "Yeah," he agreed. "We definitely need to talk."

You led him to your bedroom and shut the door. When you sat down on your bed, you noticed Dean was in front of it, starting to pace.

This was bad. This was so very fucking bad, mostly because you knew Dean almost as well as you knew yourself, and you knew that Dean only paced when he was nervous. So he was nervous about the talk the two of you needed to have, and you weren't exactly sure how to proceed.

"Y/N," Dean said, stopping his pacing to watch you closely, "what did Sam tell you? When he texted you earlier?"

The question takes you by surprise. "Oh," you say, going for nonchalance, but not sure how well you achieved it, "well, he basically just said that you and I need to talk. He said that you guys were in South Dakota anyway, and he wanted to stop by for a a day or two, and that something was wrong with you after the last time you and I were together."

Silently, Dean just nodded.

"So, Dean, we should probably talk," you say again. You're so nervous right now and aren't sure where this is going to go. You feel a little awkward, which is completely absurd; there has never been one single time since you met Dean all those years ago that you've ever felt nervous around him.

"I really enjoyed what happened the last time we were together," you say, and watch Dean closely. "It was...nice."

That word was completely inadequate, but it would work in a pinch. "I liked it, too," Dean answered, looking at you. His green eyes were watching your Y/E/C ones closely and God, you could just get lost in them.

"So I was thinking," you say, and Dean is still watching you closely. "Goddamn it, Dean, could you please sit down? You're making me nervous."

Dean nods and takes a seat next to you.

"I was thinking," you repeat, still watching him, "maybe it doesn't have to be just the one night."

"What are you saying?" he asks.

"Well," you say, and this is it, you're really going to put your heart on the line. But this is Dean, someone you'd actually do pretty much anything and everything for, "if you're willing, I'd like to try this thing out. You and me. What do you think?"

"What are you doing right now, Y/N?" he asks. When you open your mouth to ask him to clarify, he says, "I mean, are you hunting again?"

"I've been thinking about it. I just haven't done it yet because I really don't want to hunt alone. Why?"

"Sammy and I have been staying at the bunker," he says, and you already knew that, because he had told you that a couple of months ago. "We have the entire place to ourselves, so why don't you come and stay with us? We can all hunt together, and you and I can explore this thing between us. To see if it goes anywhere." He takes a deep breath and says, Y/N, can I take you on a date?"

You smile wide and look at him, "I'd love to, Dean."

That just makes him smile.


End file.
